Acetic Acid → 6-[4-(2-Dibenzylamino-ethyl)-phenoxy]-nicotinamide

HRID 130691Notes

Reaction equation

HRID 130691 reaction equation
C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[CH2:15]([NH:22][CH2:23][CH2:24][C:25]1[CH:40]=[CH:39][C:28]([O:29][C:30]2[CH:38]=[CH:37][C:33]([C:34]([NH2:36])=[O:35])=[CH:32][N:31]=2)=[CH:27][CH:26]=1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.[CH:41](=O)[C:42]1[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=1.C(O)(=O)C.[OH-].[Na+]>ClCCCl>[CH2:15]([N:22]([CH2:41][C:42]1[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=1)[CH2:23][CH2:24][C:25]1[CH:40]=[CH:39][C:28]([O:29][C:30]2[CH:38]=[CH:37][C:33]([C:34]([NH2:36])=[O:35])=[CH:32][N:31]=2)=[CH:27][CH:26]=1)[C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1

Participants

7

Reactant 5

HCID 176Acetic AcidHCID 240BenzaldehydeHCID 14798Sodium HydroxideHCID 5049666Sodium triacetoxyborohydrideHCID 444340576-(4-(2-(Benzylamino)ethyl)phenoxy)nicotinamide

Product 1

HCID 597302916-[4-(2-Dibenzylamino-ethyl)-phenoxy]-nicotinamideYield 65%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

Add sodium triacetoxyborohydride (0.2600 g, 1.227 mmol) to a stirred solution of 6-[4-(2-benzylamino-ethyl)-phenoxy]-nicotinamide (0.3058 g, 0.8802 mmol), benzaldehyde (0.092 mL, 0.905 mmol), glacial acetic acid (0.052 mL, 0.908 mmol) and 1,2-dichloroethane (8 mL). Stir for 18 h at room temperature under nitrogen. Pour the reaction into 1N sodium hydroxide (50 mL) and extract with diethyl ether (3×50 mL). Wash the diethyl ether extracts with brine, dry over magnesium sulfate, filter, and concentrate on a rotary evaporator to give the crude product. The crude product is purified by flash chromatography on silica gel eluting with 75% ethyl acetate/hexanes to yield 0.2501 g (65%) of 6-[4-(2-dibenzylamino-ethyl)-phenoxy]-nicotinamide: HPLC (30/70 to 90/10 ACN/(0.1% TFA in water) Zorbax SB-Phenyl Column 4.6 mm×15 cm×5 micron: Retention time: 8.14 minutes, Purity: 99.7%; mass spectrum (ion spray): m/z=438.0 (M+1).

Workup

  1. additionPour
  2. extractionextract with diethyl ether (3×50 mL)
  3. washWash the diethyl ether
  4. dry with materialdry over magnesium sulfate
  5. filtrationfilter
  6. concentrationconcentrate on a rotary evaporator
  7. customto give the crude product
  8. customThe crude product is purified by flash chromatography on silica gel eluting with 75% ethyl acetate/hexanes

Sources & evidence

ORD record
ord-03ebf612a2f94cd4a9c236177f63ff6f
Source dataset
uspto-grants-2008_06
Patent number
US07381719B2

Reaction notes

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